Target New Arrivals Halloween Christmas Gift Ideas Clothing, Shoes & Accessories Home & Decor Kitchen & Dining Patio, Lawn & Garden Grocery Household Essentials Baby Beauty Target Beauty Studio Personal Care Sports & Outdoors Pets Health Wellness School & Office Supplies Toys & Games Electronics & Tech Video Games Books, Music & Movies Party Supplies Gift Cards Shop by Community Target Optical Deals Clearance New Arrivals Halloween Christmas Gift Ideas Top Deals Target Circle Deals Weekly Ad Shop Order Pickup Shop Same Day Delivery Registry RedCard Target Circle Find Stores

Men’s Fall Outfits

Sponsored

23 results

Highly rated

$40.00

Men's Leo Dress Shoes with Memory Foam Insole - Goodfellow & Co™

Goodfellow & Co

4.4(447)

Black

Brown

$180.00

Timberland Men's Auburn Falls 6-Inch Waterproof Boot

TimberlandNew at

4.5(11)

$150.00

Timberland Men's Britton Road Waterproof Shoe

TimberlandNew at

4.4(95)

$99.99 - $150.00

Select items on sale

Timberland Men's Britton Falls Waterproof Chukka Boot

TimberlandNew at

4.2(10)

Sponsored

$150.00

Timberland Men's Redwood Falls Essential Chelsea Boot

TimberlandNew at

$150.00

Timberland Men's Euro Hiker

TimberlandNew at

4.6(288)

$99.99 - $119.99

reg $120.00 - $130.00

Sale

Timberland Men's Field Trekker Sneaker

4.6(89)

wheat

light taupe nubuck

$24.00 - $40.00

Select items on clearance

Men's Toby Dress Shoes - Goodfellow & Co™

Goodfellow & Co

4.4(180)

Black

$170.00

Men's Timberland Authentic 3-Eye Lug Handsewn Boat Shoe

TimberlandNew at

4.6(787)

$79.99

reg $120.00

Sale

Timberland Men's Parker Street Mid Lace-Up Sneaker

4.6(159)

black full-grain

dark grey full-grain

rust full-grain

Highly rated

$149.99 - $180.00

Select items on sale

Men's Timberland Classic 6-Inch Waterproof Boot

4.7(2347)

wheat

black

$119.99

reg $150.00

Sale

Timberland Men's Redwood Falls Lace-Up Waterproof Shoe

4.7(111)

black nubuck

dark brown nubuck

Sponsored

Highly rated

$130.00

Timberland Men's Mt. Maddsen Waterproof Hiking Boot

4.6(3010)

dark brown full-grain

medium grey nubuck

black full-grain

$119.99 - $180.00

Select items on sale

Timberland Men's Britton Falls Mid Waterproof Boot

TimberlandNew at

5(5)

Highly rated

$130.00

Timberland Men's Lake House Classic 2-Eye Boat Shoe

4.6(914)

medium brown full-grain

$170.00

Men's Timberland Originals 6-Inch Boot

4.4(1220)

medium brown

$99.99 - $150.00

Select items on sale

Timberland Men's Britton Falls Chelsea Boot

TimberlandNew at

5(1)

$180.00

Timberland Men's Britton Road Mid Waterproof Chukka Boot

TimberlandNew at

4.8(40)

black full-grain

$190.00

Timberland Men's Britton Road Mid Lace-Up Waterproof Boot

TimberlandNew at

4.6(60)

rust full-grain

$79.99 - $120.00

Select items on sale

Timberland Men's Parker Street Mid Sneaker

TimberlandNew at

5(2)

Sponsored

$220.00

Men's Timberland Heritage 6-Inch Waterproof Boot

TimberlandNew at

5(2)

$109.99 - $150.00

Select items on sale

Timberland Men's Redwood Edge Mid Boot

TimberlandNew at

2(2)

$160.00

Timberland Men's Mt. Maddsen 2.0 Hiking Boot

TimberlandNew at

5(5)

Explore more of what’s going on right now

Get top deals, latest trends, and more.